799781-89-8

Upstream product

• 799781-87-6 ethyl-2-[2(RS)-cyano-(2(RS)-(1(R)-phenylethyl)amino)cyclohex-1(RS)-yl]ethanoate 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 24731-17-7 ethyl 2-(2-oxocyclohexyl)acetate 
• 801297-18-7 trans-ethyl-2-[2(R)-carbamoyl-(2(R)-(1(R)-phenylethyl)amino)cyclohex-1(S)-yl]ethanoate 

Relevant academic research and scientific papers

Stereoselective synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3- azabicyclo[4.4.0]decan-2,4-dione hydrochlorides: Bicyclic glutamic acid derivatives

Asymmetric synthesis of (1R,2S)- and (1S,2R)-1-amino-cis-3-azabicyclo[4.4. 0]decan-2,4-diones has been achieved. The underlying second generation asymmetric synthesis proceeds via a Strecker reaction with commercially available (R)-1-phenylethylamine (1-PEA) as chiral auxiliary, TMSCN as cyanide source and racemic ethyl 2-(2-oxocyclohex-1-yl)ethanoate. A ring closure addition-elimination reaction between an amide nitrogen and the ester functionality leads to the 1-amino-3-azabicyclo[4.4.0]decan-2,4-diones. The absolute configurations of the title compounds have been assigned based on detailed NMR-spectroscopic analysis and X-ray data. Graphical Abstract.